Fw. Lichtenthaler et al., STUDIES ON KETOSES .7. 5-(ALPHA-D-GLUCOSYLOXYMETHYL)FURFURAL - PREPARATION FROM ISOMALTULOSE AND EXPLORATION OF ITS ENSUING CHEMISTRY, Liebigs Annalen der Chemie, (9), 1993, pp. 967-974
An effective, practical, large-scale adaptable procedure has been deve
loped to selectively dehydrate the fructose portion of isomaltulose [g
lucosyl-alpha(1-->6)-fructose] (6): heating in DMSO in the presence of
a strongly acidic ion-exchange resin generates alpha-D-glucosyloxymet
hylfurfural (''alpha-GMF'', 3), isolable in yields up to 70%. A variet
y of ensuing reactions have been exploited concerning the generation o
f products with industrial application profiles such as aldol-type add
itions to the dicyanovinyl (16), nitrovinyl (20), and benzoylvinyl (21
) derivatives, or to the polymerizable unsubstituted vinyl compound (2
5) and the GMF-acrylic acid (22). Oxidation to GMF-carboxylic acid (11
) and reductive amination to GMF-amine 8 can be carried out without af
fecting the hydroxyl groups in the glucosyl portion; esterification of
11 with long-chain alcohols and N-acylation of 8 with fatty acid chlo
rides provide novel surfactants in which hydrophilic and hydrophobic p
arts of the molecule are separated by a heteroaromatic spacer.